Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 178482518, compound

A solution of 2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine (from the dihydrochloride, 4.27 g; 14.0 mmoles) in 30 ml of methanol was added to a well stirred suspension of 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide (2.50 g; 14.0 mmoles) in 250 ml of methanol at 10°. After 15 minutes at 10°, the solution was cooled to 1° in a cooling bath and anhydrous methylamine was bubbled into the solution for 10 minutes. The reaction mixture was evaporated under reduced pressure and the residue placed on 60 g of silica gel and chromatographed using a gradient elution of methylene chloride-methanol. The appropriate fraction containing 4.53 g of product was placed on 80 g of aluminum oxide and rechromatographed using a gradient elution of ethyl acetate-methanol. The appropriate fractions were combined and evaporated to give a foam which crystallized from methanol to yield (2.38 g) of the title compound, mp 196°-198° (dec).

1. temperaturethe solution was cooled to 1° in a cooling bath
2. customanhydrous methylamine was bubbled into the solution for 10 minutes
3. customThe reaction mixture was evaporated under reduced pressure
4. customchromatographed
5. washa gradient elution of methylene chloride-methanol
6. additionThe appropriate fraction containing 4.53 g of product
7. customrechromatographed
8. washa gradient elution of ethyl acetate-methanol
9. customevaporated
10. customto give a foam which
11. customcrystallized from methanol

ORD record

ord-7df0b8f14b984918bdecb3c6662b50e7

Source dataset

uspto-grants-1983_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04380638